Phenylacetylene → HCID 19090127, compound

HRID 1463308Notes

Reaction equation

HRID 1463308 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](I)[CH:4]=[N:3]1.[C:8]1([C:14]#[CH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(NC(C)C)(C)C.C(OCC)(=O)C.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:15]#[C:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[N:3]1

Participants

8

Reactant 3

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 27347731-Methyl-4-iodo-1H-pyrazole

Product 1

HCID 19090127HCID 19090127, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 7912DiisopropylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-4-iodopyrazole (208 g, 1 mol) and phenylacetylene (112 g, 1.1 mol) in diisopropylamine (2 l) are added, under nitrogen, copperiodide (2 g), triphenylphosphine (0.1 g) and bis-(triphenylphosphine) palladiumdichloride (0.5 g). The mixture is kept during 3 hours at ca. +35° C. and then heated for 1 hour at +90° C. The cooled reaction mixture is diluted with ethyl acetate and filtrated. Concentration of the filtrate and distillation yields the title compound: b.p. 116°-118° C./0.3 mbar, m.p. 70°-72° C.

Workup

  1. temperatureheated for 1 hour at +90° C
  2. customThe cooled reaction mixture
  3. filtrationfiltrated
  4. distillationConcentration of the filtrate and distillation

Sources & evidence

ORD record
ord-1b52132531514c289474cd56ed19290d
Source dataset
uspto-grants-1994_04
Patent number
US05300521

Reaction notes

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